


Winter Wonderland

by LaSwire25



Category: Gilmore Girls, Supernatural
Genre: AND GAY, And Now For Something Completely Different, And has secrets, Angst and Tragedy, But Henry is Dean's biological father, Corporal Punishment, Dean Winchester is Sam Winchester's Parent, Dean is a very young Dad, F/M, Family Drama, Family Feels, Family Secrets, Gen, Henry is British, John and Henry are cousins, John is Dean's Dad, John is a good father, M/M, Not Canon Compliant, Overprotective Dean Winchester, Teen Pregnancy, Teen Romance, The Slowest of Slow Burns for just about everything, Traumatized Dean Winchester, Traumatized Sam Winchester, Very strict Dean
Language: English
Status: Completed
Published: 2018-11-27
Updated: 2018-11-27
Packaged: 2019-08-30 03:45:23
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,337
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16757050
Author URL: https://archiveofourown.org/users/LaSwire25/pseuds/LaSwire25
Summary: Sam Winchester is the new student at Chilton Prepatory School for privileged teens.  Homeschooled for years following a traumatic event, he's an awkward and shy mystery to his fellow students.  Little do they know that he's not just another rich kid, but a scion of British nobility.  Rory Gilmore is Chilton's star pupil.  The daughter of a Hollywood star father and the enigmatic owner of the popular local cafe for a mom, she's quiet but content with her life and steering clear of the drama of high school dating.Until she meets Sam.An out of control house party is the catalyst for secrets from the past to come bubbling back to the surface.  As Sam and Rory start to get closer, they will discover things, not only about each other, but themselves and their families as well.Each chapter is told from the POV of a main character.  A million more tags to be added in time.





	Winter Wonderland

Rory

They were fighting again.

Not that this was anything new. After the first few months of sickeningly sweet newlywed bliss almost four years ago, the inevitable marital arguments had become increasingly louder and more frequent. Even at twelve years old it hadn’t take long for me to see that Sherry, my vapid and reluctant stepmother, was far more interested in my father’s celebrity status than she actually was in my father himself. Her years as a borderline alcoholic social climber had not been kind to her looks. Personally, I think she should be grateful that my dad, who is young, good looking and wealthy, would even be interested in her in the first place.

Standing outside the door to their offensively opulent Georgian style mansion as the heated battle inside escalated, I was debating on whether or not I should just leave and go back home. Besides the raised voices, there was a cacophony of noises attributed to, I assumed, clean up from my step-sister’s latest house rave. 

Maybe it was my stubbornness that kept me standing on the white pillared porch instead of driving off like a coward. Mom says that my pig headed attitude is my most unflattering personality trait, and she would know since I get it from her, but she also grudgingly admits that it’s probably one of the things that are going to help me succeed in life someday. 

_Thanks, Mom_.

Above my head I heard another loud bang and then a screech that could only belong to Georgia, my banshee of a stepsister. I kind of suspected that the most important of the qualities my dad might have once found attractive about Sherry was the fact that she had a daughter just about my age. Some well meaning but genuinely demented part of the heavy baggage that comprised his _Dad Guilt_ probably thought that giving me a sibling would be a good thing for me. 

It didn’t seem to matter that Georgia and I were nothing alike and had absolutely nothing in common except our mutual dislike for each other. 

I really had no desire to have her in my face this morning either, and just thinking about it had me turning around and heading back to Daisy, my bright yellow Audi Cabriolet. It was a beautiful Saturday morning, all blue sky and white puffy clouds, and I could think of a million other more enjoyable things to do rather than going into that house and dealing with _Blonde Medusa_. 

_Like getting a root canal without Novocain_.

Annoyingly, I only made it down to the last step before I stopped. The simple reality was that I hadn’t seen my dad in almost a month, and besides the bonus attraction that my mere presence today was bound to make the vein in Sherry’s temple throb, to be honest I just really missed him. 

Dad means well, but his large sack full of promises rarely manifest into actual time spent together. We'd already canceled plans last month for the weekend whitewater rafting trip that he had been promising me forever, as yet another attempted consolation prize for the skiing trip that he canceled on me right after Easter when he was called back to California for some last minute re-shoots. 

What was I supposed to do when his blatantly raw guilt was so heavy he couldn’t even look me in the eyes while we Skyped? So I told him that I understood, just like I always do. It wouldn’t change anything to have me beat him over the head with these things. I already knew he felt bad enough without having my disappointment thrown at him as the cherry on top of the absentee parent sundae. This was just how our time together usually worked out. 

What’s that saying about good intentions again?

Dad was always full of good intentions. The probably was his delivery. Or, more to the point, the lack thereof.

When I was ten I had refused to go visit him over winter break when he’d missed my school’s Father-Daughter Snow Ball after promising for weeks that he would be there. Mom and I were already at the salon having my hair done when he finally called and said he'd missed his plane because shooting was going long, and I had cried all night, my product glossed curls still stiff and smelling like hairspray, and my perfect ridiculously expensive dress flung in a heap on the floor of my room. It was one of the few times that I can remember Mom actually being angry with my father and I guess that is what had finally been the last straw in our long distance relationship with him. 

Although my parents haven’t been together since Mom was pregnant with me, they’re still good friends, with none of the standard hostility or awkwardness that I see with so many of my friends’ divorced parents. Other people we knew would use their kids as weapons against each other, and not realize or just not care what it did to them, but not my parents. I’ve always been lucky in that respect.

After that, Dad finally decided to move back to Connecticut to spend more time with me and commute for jobs. I loved him for making the gesture, because he always seemed to genuinely love the Hollywood lifestyle. Mom had been cautiously optimistic about it, but she did warn me I shouldn’t get my expectations up too high, and over time I’ve learned to do just that. Dad’s work is still mainly in Los Angeles, and he’s away far more than he’s home. It’s taken a lot of understanding and compromise to try and make this life work for us.

Reminded of how often I’m the one expected to compromise, my temper flared up to an unusual level and I stomped back up the steps. Today was supposed to be our day together and I refused to let Georgia or Sherry’s latest hissy fit interfere again. They took up enough of his time as it was, and quite frankly, I’m sick of it. This was probably going to be the last time we would have together for two months since he was leaving in a few days for a publicity tour for the new movie. Maybe I could sweetly suggest that Sherry take _Booze Barbie_ for another rhinoplasty consult before Georgia’s abnormally sharp nose fatally stabbed some innocent bystander.

I ignored the sounds of the inevitable train wreck that the large oak door was failing to conceal. Even though this is technically supposed to be my house too, I usually knock, just out of courtesy. Only today I was in no mood to be polite, so I waltzed right in and immediately almost waltzed right back out again. The whole entry looked like a war zone and there were half a dozen uniformed cleaners bustling around with mops, brooms and trash bins. No wonder everyone was screaming. It looked like a ridiculous scene out of an old Mel Brooks picture.

The entire left wall of the entry was lined with full-to-bursting trash bags, and as I stood there shocked by the chaos, two men were carrying out the formerly pure white sofa that Sherry paid over twenty thousand dollars for last summer. I gaped at it wide eyed, because I clearly remembered the horror on my father’s face when the bill arrived. Currently, it was boasting an enormous dark pink stain that covered almost the entire left side, and I caught myself idly wondering which one of Georgia’s signature party cocktails had such an obnoxious color and exactly how much had to be spilled to ruin that much fabric.

I slowly made my way towards Dad’s media room, apologetically dodging the growing team of cleaners that seemed to keep coming out of nowhere. Like a never ending parade of dizzy and frazzled worker bees that wanted out of a hostile environment as soon as possible. 

As I got closer, I could hear the actual conversation now, instead of just the indistinct buzz of heated screaming. I wasn’t suicidal enough to break into the middle of what sounded like the precursor to barroom brawl when I knew how many things inside the room had the potential to become angrily flung projectiles, which was Sherry’s reaction of choice. Instead, I flopped down on the settee just outside the closed door, knowing from experience that this could be a while, and pulled out my current book to entertain myself while I was waiting. 

Because there were so many people rushing around, it took me a moment to realize that the matching settee across the hall from me was already occupied by Martin, my Dad’s long suffering attorney. I was momentarily embarrassed on my father’s behalf to have his household’s dirty laundry aired in front of so many people, but then I reminded myself of just how many times Martin had been dragged into our regular family drama. He smiled at me in greeting and, with his eyebrows raised, he just shook his head before returning to the pile of notes he had on his lap.

“She’s out of control, Sherry,” I heard Dad say, not for the first time. “We’re lucky none of those kids died last night.”

Reverberating against the walls, a long drawn out groan gave all the indication I needed to know just how not seriously my stepmother was taking the situation.

“You don’t have to be so dramatic, Christopher. The cameras aren’t rolling right now.”

I snorted a little, used to this comeback by her. She never had a good response to my father’s irritation at her daughter’s escapades and Sherry seemed to think that she was being witty by poking fun at his profession. Martin didn’t react. He couldn’t help hearing them, they were being so loud, but I guess lawyers learn to block out their clients’ private lives as a matter of self preservation.

“She’s getting on that plane this time,” Dad said, in his _I’m perfectly reasonable but deadly serious_ tone. The one he frequently used when Sherry’s black AmEx bill arrived, with its pages thicker than some school books I had. 

“It’s already fueled and waiting.” 

Sherry laughed, and I heard the sound of ice cubes clinking in a crystal glass and shook my head. 

_Jeez, Sherry. It’s not even ten AM_.

“My daughter isn’t going anywhere,” Sherry snarled. “And if she were, it would be up to me and her father to make that decision. Not you!”

“Great!” Dad was sarcastically laughing now as well. “Where’d you find him this time? Vegas? New Orleans? Prison?” He chuckled a little more and I heard hands slapping on wood. “She needs help, Sherry! Why can’t you see that?” 

Because my stepmother didn’t want to believe half of the bad things about her daughter. I don’t know if she was just in denial, or truly couldn’t see what a hot mess Georgia was. Honestly, there were times I was sure she simply didn’t care as long as it didn’t interfere with her generous monthly expense account and her ladies lunches.

“Not everyone is an addict, Christopher!” Sherry retorted, with a condescendingly vicious tone to her voice. As if she was explaining something incredibly obvious to someone she considered feeble minded. “Just because you are, doesn’t mean that my daughter is!” 

_Ouch_ I flinched hearing that. I’m sure my dad did too. He didn’t hide his past, but he wasn’t proud of it either. Martin looked at me sympathetically, and I tried to smile, but I could feel the blood rush to my face. It’s not like Martin didn’t know, considering how many times he had wrangled the legal and publicity issues that my father’s former cocaine habit caused, but even still, it wasn’t something we talked about openly and I was embarrassed on my dad’s behalf because he’s worked so hard to put it behind him.

Abruptly, the door flew open and my father stormed out into the hallway, Sherry rapidly following him. 

“We are not finished, Christopher!” 

Dad didn’t break stride as he approached Martin. 

“Oh, yes we are,” he bit back, determined as he threw her a poisonous glare, only then seeing me sitting next to the door. 

His face fell almost immediately and a million emotions passed in his eyes. Shame, sadness, regret and defeat, before finally softening as he sighed and ran the fingers of his right hand through his thick light brown hair. I could see it on his face that he was just now remembering that we had plans.

“Just a sec, Martin,” he said apologetically, before coming back over to me and hunkering down in front of the settee. He took my right hand gently between both of his and kissed me on the forehead. 

“Hey, sweetheart.” 

Sherry stopped short next to both of us and the pure hatred in her eyes as she saw me was nothing new to me, having been on the receiving end a thousand times when she was sure my father wasn’t looking. I didn’t care. As far as I was concerned, I felt nothing but pity for her. She would always be the kind of person who hated themselves so much that they could never be truly happy.

“Rory, this isn’t as good time. You’ll have to come back later,” she barked, raising a perfectly manicured hand to her forehead and looking completely put out. _Maybe if she didn’t start boozing after breakfast, she wouldn’t be feeling so rough_ , I thought with less charity than my mother raised me to have for others.

For a second I expected my peacemaker father to calm her down, as he had a habit of doing when she was unkind to me, but he clearly wasn’t in the mood for her nonsense today. He kissed me again and stood back up, towering over his wife with his full height and exuding no desire to play nicely.

“This is my daughter’s home, Sherry,” he hissed. “She can be here whenever she wants, for as long as she wants. If you have a problem with that, you can be the one to leave.”

I think Sherry and I both skipped a breath when we heard that. My father didn’t speak that way to anyone. Certainly not to her, and certainly not in front of anyone, including me. Dad was always the kind of person to trip over himself trying to make everyone else relax when there was tension, and even Martin seemed shocked.

Dad didn’t back down an inch, even as Sherry’s face went pale, and inwardly I was cheering him on for finally standing his ground. 

“Clock’s ticking,” he reminded her, his lips pressed firmly together and his eyes gray, stormy and cold. “Her plane leaves in an hour. She’s going to be on it, or I wash my hands of everything. And I do mean _everything_.”

Sherry was blinking rapidly, making queer little gasping sounds as if she was trying to speak but her mouth wouldn’t cooperate. I knew as well as she did that Martin had insisted that she sign an iron clad pre-nup, and while my father wasn’t an unkind man and she wouldn’t necessarily be poor in the event of a divorce, she wouldn’t have the lifestyle that she had happily become accustom to living.

More importantly for her, neither would Georgia. 

Honestly, I hadn’t realized that things had gotten to the point where Dad would consider splitting with her. They didn’t really talk all that much in front of me, but I couldn’t help but feel a little relief on my father’s part that this unhappy marriage might be coming to an end at some point in the not too distant future.

Dad stared her down for another minute and then walked over to Martin and they started speaking very quietly. I was uncomfortable enough after witnessing such a private exchange, and I really didn’t want to get another glare from my stepmother, so I feigned interest in my book until I heard the clicking of Laboutin heels as she climbed up the marble staircase at the end of the hallway. Dad and Martin were now heading towards the media room, but my father stopped for a moment to sit and put his arm around me.

“I’m sorry you had to see that, sweetheart,” he apologized sadly. “Georgia needs help, and if I don’t do something, her mother certainly won’t. I’m worried about what will happen to her.” 

I knew that already, actually. Around our school, Georgia’s parties were infamous, and my mom would have never allowed me to go to one. Even if I had been invited, which, I never was. In theory, Sherry was suppose to chaperone but somehow she always seemed to have obligations in the city while the house parties were held, and my father was gone too frequently to really have a true understanding about how often they took place. Like this one. Dad had only flown back home this morning, and I couldn't even begin to imagine what had been waiting for him when he landed.

“It’s fine, Dad,” I assured him, because he didn’t need any more stress. “Are you okay?” 

He laughed sadly and pulled me into a tight embrace, and I couldn’t help the automatic feeling of comfort and safety that filled my heart as soon as his arms encircled me. No matter how old I grew, there wasn’t anything that made me feel more loved than getting held by my dad.

“It’s just like you to be worrying about me right now,” he murmured, his mouth buried against my left temple.

That was the moment that I knew that our plans for the day were well and truly out the window. Of course I began to suspect as much the minute I pulled up to the house but, on some level, the hopeful little girl inside me wanted to be put first for once. It was selfish of me to want that, considering that there were more critical events taking place in my father’s house today, but it didn't change the fact that I wanted it.

As much as I disliked Georgia, if Dad was serious about getting her some help then, at least for his sake, I needed to be supportive. Even if it came at the cost of my time with him.

Which it always seemed to.

I pulled away from his embrace gently, because I didn’t want him to feel the tension that was threatening to take over my composure. I already knew that having to disappointment again was upsetting to him, and right now he didn’t need more on his already full plate. I loved my dad enough that I couldn’t willingly add to his burdens. He was just doing the best he could.

“Raincheck?” I asked, plastering the sweetest smile I could manage on my face.

For a brief moment, his eyes went sad and stormy gray, and he looked far older than his youthful thirty-four years.

“Aw, sweetie, I…,” he started, but I just held my hand up and leaned up to kiss him on the cheek.

“It’s okay, Dad,” I assured him again. “Do what you have to do. I don’t mind. Really.”

I was lying, of course, and on some level we both knew it. We also both knew there was no way around it today either. He opened his mouth again, to most likely offer me another unnecessary apology, but before he could get a word out a shrill cry echoed from the upstairs hallway, and judging by the thundering noise of several objects being thrown around, Georgia had just been informed of her impending departure for rehab.

She really was a lot like her mother.

Dad and I just looked at each other for a few seconds before he gave me another quick hug, tiredly whispering “I love you, baby,” as I closed my eyes and inhaled his distinctive _Dad smell_. Tightly gripping my fingers in the back of his sweater before I forced myself to let go. After one more apologetic look, he charged up the stairs like a man heading into battle. I didn’t envy him.

Seeing his client take off again, Martin sat back down, still patiently waiting at his post. His dedication seemed to go far above and beyond the normal duties of a personal attorney, and I couldn’t help but wonder exactly how much of his annual income came from the multitude of dramas in my father’s life that needed constant fixing. He’d been a steady part of our lives from the time that my father signed with his long term studio. To the point that Martin opened a local office and did the necessary work to admit him to the Connecticut Bar when Dad chose to move back here.

I had a startling thought that Martin was just about the closest thing that my dad had to a friend, now that his coke fueled party days were behind him. Back then, there was never a shortage of strangers hanging around Dad’s various residences, but ever since he got clean and slowed down, the nameless throng had evaporated back into the unknown vapor from where they'd come from. A horde of opportunists that had moved on to the next celebrity addict like a swarm of locusts.

I know that it was a development that my mother happily welcomed. Aside from being pleased that Dad overcame the destructive habits that played a large part in their breakup, she never trusted the people that were more than happy to live off of my father’s fame and fortune, like so many in the shallow, plastic world of Hollywood.

As I grabbed my discarded book from the settee I had been using, I finally noticed a large pile of random items cluttering the top of the sideboard to the right of where Martin was sitting.

“What’s all that?” I asked him, not really expecting him to have an answer for any reason other than the fact that he had arrived earlier than I had.

He looked up from his notes and idly glanced at the pile. “I think they’re things that were left behind by last night’s attendees,” he said dismissively. It didn’t take a mental giant to discern exactly how he felt about the kids that had run rampant through my father’s house and the parents that allowed it. He also probably didn’t appreciate being dragged over here first thing this morning and made to sit around and wait while Dad corralled his wife and stepdaughter either. 

Honestly, I probably wouldn’t have given the pile a second thought if I hadn’t seen the unmistakable familiar blue perched on the top.

Logically I knew that I couldn’t really be seeing what I thought I was, because I felt sure that the owner of the custom made Tardis phone guard wasn’t the kind of person that would have come to Georgia’s party. Or, at least, I thought he wasn’t.

Although, as I crept closer to the table, it became readily apparent that I was mistaken. I knew that particular phone as well as I knew my own. Simply because it had been the conversational ice breaker for the fledgling friendship I had started with the adorably nerdy guy that it belonged to. A fledgling friendship that I had been quietly hoping might develop into something more, if I was to be perfectly honest with myself.

I was furious for all of a nanosecond thinking that I'd been completely mistaken with his character. Having thought that he was a better person than the overly privileged obnoxious jerks that tended to populate my stepsister’s inner circle of friends. But I chastised myself just as quickly, because I did know better than that. Although I'd only known him for a month, it didn't take a genius to see that there wasn't a self absorbed bone in Sam's beautiful body. He was almost painfully shy to the extreme, and not at all like the guys that thought the sun rose and set around them.

I tried to be casual as I reached for the phone and, to his credit, Martin ignored me even though it was fairly obvious that he saw exactly what I was doing. I appreciated that, for reasons that I couldn't quite explain.

The phone was dead, but I didn't need any more confirmation that it belonged to Sam. There was a slight nick on the upper right hand corner from landing on the pavement in front of our school when he rushed to help me pick up an armful of books that I had dropped in front of him like the clumsiest of fools that I was. Too stupidly romance novel level mesmerized by his beautiful hazel eyes and mile deep dimples to pay attention to what I was doing. My face had flushed hot with embarrassment, but he just laughed in a way that I instinctively knew wasn't at my expense while gathering my books in his own arms, and he smiled wide, showing off a set of perfect dazzling white teeth, when all I could do was geek out over his phone guard.

The only polite thing to do would be to return it to him, right? With it being dead, he probably didn't even know where it was, and if he was like any other person my age he was probably freaking out over not having it. And so what if it just so happened that I knew where he lived? The school _did_ have a student directory for a reason, after all.

Just because I might have driven past the gate outside his house once or twice, it didn't make me a stalker or anything. Autumn is a beautiful time of the year. The area he lives in is extremely scenic, and it's a free country.

Yeah, I don't buy that either.


End file.
